From One Freelancer to Another – Tactical Tips and a Free Tech-Support Chatbot
If you tell yourself, “I’m SO bad with technology,” this blog is for you.
First off, stop saying that. Not a boss vibe.
As a freelancer, you can’t side-step tech challenges – and avoiding them can (and WILL) cannibalize your business.
The entrepreneurs you look up to most? They’ve had late nights on the laptop trying to set up their website. Troubleshoot automations. Figure out why their payroll didn’t go through. Arrange the landing page blocks in the right order. Send the invoice the right way.
It’s not sexy, but seriously – we’ve all been there.
So how do we “been there”…but faster? Tech troubles have a nasty way of eating your energy and motivation in huge chunks. Reducing the tech issues and the time it takes to resolve them has major ROI.
Over the years, I’ve had loads of tech troubles that had me in tears. There isn’t really a secret to making things easier other than:
You need to commit to believing it’s figureoutable (trust me, it is).
You’ve got to act like it by putting in the work.
But here’s the really, really great news – 99.9% of the time, someone else has figured it out. It’s just a matter of finding how they did it most efficiently.
I’ve got 8 tactical tips on what’s helped me go from hours to minutes when troubleshooting.
But better than that – I built you a free on-demand chatbot that can give you customized tech support tailored for tech conundrums that come up as a freelancer.
Let’s go!
1. You’ve Got To Stop Avoiding Them (That’s What’ll Give You Power As An Entrepreneur)
As a freelancer, you don’t get the option of sidestepping technology. It’s a part of the deal.
Thankfully, you don’t have to make it complicated. You don’t have to master all the software or become a tech guru.
But your unwillingness (or procrastination) with facing tech challenges will directly limit your ability to grow and make money.
I’m talking about things like:
Building your own website
Learning how to find and understand backend analytics
Exploring automations to make your systems easier
Using search engines efficiently (like Google)
Using long language model AI (like ChatGPT)
Even just figuring out how to adjust the font on your Google Docs
Early on, I loved telling myself that I wasn’t great with tech. I used this cop-out partly because my brother literally graduated at 18 with his Bachelor’s degree in computer science. How could I compare to that?
Mostly, though, it felt like a justifiable Band-Aid when things got too frustrating. Why push through when I could ask someone more tech-savvy… or just give up?
Well, as a business owner, you’re the boss. It’s your job to figure things out. The person paying for your unwillingness or procrastination with tech issues is YOU.
Thankfully, part of being a great boss to yourself is making things easier for yourself, even if you can’t avoid facing tech challenges. Let’s talk more about those.
2. Dumber People Have Figured Out the Tech Issues You’re Avoiding
Perseverance will take you a lot farther than skill when it comes to tech. There are people way less savvy with technology who are doing the things you wish you knew how to do.
It's not because they're "young" or "good with computers." It's because they stuck with solving the problem.
They were willing to:
Find some low-quality video on YouTube where a nice professor explains how to work Excel
Commit to an hour of the old "plug & play," trying out different things until something worked
Reach out to a friend or acquaintance who does stuff like what they’re trying to accomplish
Haunt some Reddit forums
Berate Google/ChatGPT/etc. until it gave them something that worked.
Thankfully, now you can get AI to do a lot of that research for you and compile it into a nice step-by-step guide of what to do next.
The “secret” is persistence. It’s the knife in procrastination’s gut. It’ll always trump skill in Freelancerville. Stick with it, and you'll be surprised at how many issues weren’t that hard to solve.
3. Start Simple and Upgrade Over Time
Online freelancers have to use some software to get the job done. And there’s a ton of software that would be happy to take your money to help support your business.
I was totally overwhelmed in the beginning.
What’s the right website hosting platform?
Invoicing software?
Email marketing platform?
Course hosting platform?
Do I get them all separate, or try out the ones that integrate lots of different functions?
The major issue was that I treated these decisions like they were irreversible.
You're not picking a life partner, your retirement investments, or a degree from a university.
Software decisions are extremely reversible. There’s nothing stopping you from using one website hosting platform for a year and then switching to something different if you find a better fit. Great businesses do it all the time.
What I didn’t understand as a newbie was that savvy business owners have no problem switching up their systems or software when they see it’ll make things easier.
You can do this with both the software you’re using and the business systems you have in place.
Change how you onboard clients if you found something more efficient. Cancel your invoicing software subscription if you discover a better one. You’re not getting points docked from some Business Police.
A big reason I was stressed about picking the “right” technology was because I thought I needed something that could grow with me.
While this CAN be useful, it’s a lot more useful to work with technology that will actually get you using it. You don’t have to learn on a stickshift every time you’ve got a new technology to navigate.
In the beginning, you won’t need all the bells and whistles. You might later on, but that doesn’t mean you need the fancier software from the start.
Most software technology can be divided into two rough categories: user-friendly with fewer features and more complex with a steeper learning curve.
In my experience, if you’re starting out, there’s no shame in using something user-friendly. It boosts your confidence and strengthens your foundational skills faster.
Your software doesn’t make you “more professional.” Your integrity does. People build 6-7-8 figure businesses on Gmail and Google Docs.
4. Don’t Reinvent Resources That Are Already Available
You’re not the only one who has tried to figure out the tech problems on your plate. People have created TONs of resources that’ll make things faster.
I know, the emotional strain of figuring out your own tech troubles hurts a lot. That’s why business owners shell out thousands of dollars to get someone else to fix tech problems for them.
I’ve seen countless beginner freelancers on forums looking for someone to help with their website. Not because they could afford it or were strapped for time – but because they were intimidated by trying to figure it out themselves.
Use the resources available to you:
Call up customer support
Go to the software website FAQ or blog
Do a Google search
Find a relevant blog post
Watch tutorial videos on YouTube
Ask questions on Reddit forums (or creep around to see what people already said)
Reach out to a friend for some fresh eyes
Ask ChatGPT for help (my ultimate favorite!)
There are good reasons to pay someone to handle your tech struggles, but in the beginning, being intimidated is a terrible reason to outsource tech.
You likely don’t have the budget for it, and the perseverance muscles you build by tackling these challenges will flex in other areas of your freelancing.
5. Block an Hour to Tackle Tech Issues
For most of us, dealing with technology isn't stressful because it takes a lot of time. It's because we have trouble tolerating the emotional discomfort of figuring out the unknown for more than five minutes.
Everything gets so much more frustrating because a tech problem usually stands directly in the way of a bigger task we need to complete. We'd much rather be dealing with the task on the other side, but now we have two tasks to worry about.
Another thing that escalates our emotions is this fear that we ultimately won't be able to figure out the problem.
As a recovering perfectionist, this mindset was especially popular in my head.
A mentor once gave me a great piece of advice: if you’ve got a problem in your business that’s totally overwhelming, schedule one hour just to work on it.
It takes away some of the pressure of getting to the task on the other side.
It gives you the margin to take your time figuring something out instead of pressuring yourself to squeeze it in between other tasks.
Block out an hour. You’ll make a ton of progress. And you’ll see how much a single issue was congesting your business.
6. Sometimes It’s Hard Because You’re Making It Harder For Yourself
You don’t get points by making things more “fancier” (e.g. more complicated). Simple is king.
And alot of the time, the simplicity you’re looking for with tech is living outside the box.
Let’s say you’re having trouble figuring out how to use the “send proposal” feature on your client management platform. You got Honeybooks or Dubsado or whatever, and you’re super excited to have a platform that’ll do it all!
You’ve got an interested lead because you just had a call. But you’re getting stuck on the proposal. You can’t get it to send a test to yourself to see if it works. It’s hard to write, you don’t know if you’re formatting it the way you’re supposed to, and you’re really stressing out because you don’t want to lose this potential sale.
Experienced business owners know there are loads of potential solutions to “unsolvable” problems.
Call customer service
Look up a video tutorial
Check out the company’s FAQs
Ask ChatGPT how to set it up on that specific platform
Just send what you have as is and let the chips fall so you can course correct later
Opt not to use that platform for the proposal and simply send it as an email
Scrap the proposal entirely and treat the contract as the proposal that they’ll either accept or decline
And that’s just a few options
If you’re feeling overwhelmed and out of ideas for the next step, I can’t recommend talking to a friend enough. And if one isn’t available for a brainstorming session, use AI.
7. Save & Create How-To’s for Recurring Tech Struggles
Tech troubles are inevitable. But the good news is you’re going to encounter many of the same ones repeatedly.
Tech issues tend to be front-ended problems. Once you figure out how to solve an issue once, it doesn’t have to be a problem anymore.
One of the biggest timesavers you can create in your business is a simple document that acts as a link library. These links could be to:
A YouTube video that addresses a recurring problem (thank you, Squarespace and Flodesk tutorial people. You’re my hero.)
Another document where you wrote down step-by-step instructions for a complicated process (I frequently reference my Google Doc shortcuts)
A loom you created for yourself walking through something technical (I have lots of these, like the SOP for creating an email signup banner in Flodesk then plugging in the code to Squarespace)
Label these solutions with lots of keywords so that it’s easy to find them when you need them.
You might only have five links that you constantly refer to, but that’s a substantial amount of time and mental energy saved.
8. Making Tech Easy for You Makes It Easy For Clients
User-friendliness gives you a ton of momentum as a beginner or when you're in an overwhelmed season. But another amazing benefit of making things simple is that it makes it easier for your clients.
A process that’s easy for a client to navigate will always improve their customer experience. You’ll impress clients with how easy it is to work with you, not by how fancy you make things.
If your email, a Google doc, or a spreadsheet can handle an area of your business, try it out first. There’s plenty of million-dollar businesses that keep their clients organized with these basics.
Plus, if you want to upgrade in the future as your business needs get more complex, you’ll want to be familiar with the basics of a system. For example, if you’re brand new to keeping your leads and your outreach efforts organized, a nifty customer relationship management (CRM) is not going to magically work better than a basic spreadsheet.
Are the fancy softwares helpful? Sure they are, that’s why they’re made. But they were built to solve complex problems, like overwhelming amounts of data and building automations.
There’s a TikTok that lives in my head rent-free that perfectly illustrates this.
An HR rep, on a Zoom call, was trying to figure out a manager's thought process on adding a QR code to an email. It had caused a lot of problems because employees tended to check their email on their phones – but they needed their phone to scan the QR code.
At the end, the HR rep bluntly asked: “Is there a reason we didn’t just include a clickable link in the email instead of a QR code leading to a clickable link?”
You have no idea how many business owners complicate their systems by over-fancifying technology like this. Keep it simple, and you'll improve both your efficiency and your client's experience.
That Tech Snag That’s Stalling Your Business?
That’s The Exact Place Your Peers Are Giving Up.
Keep Going.
Dealing with tech is some of the least glamorous but most common business tasks out there.
Remember, when things get hard with technology, it's the exact place where most people stop. Most of your competition won’t push through these tech struggles, which gives you a major head start if you choose to persevere.
All boiled down, here’s what I want you to know:
Face tech troubles head-on. Avoiding them limits your growth.
Dumber people have overcome the tech challenges you’re facing with persistence.
Start simple with user-friendly software and upgrade as you grow.
Use resources that are already out there, like customer support, YouTube, and AI.
Schedule an hour to tackle that one tech issue.
Simplify your approach to prevent self-imposed complications.
Create a doc as a library of resources for recurring tech problems.
Make tech processes easy – your clients will love it.
Lemme tip my hand. I really believe that using AI to get step-by-step help with your tech troubles is one of the best ways to save your sanity (and time!) as a freelancer.
It’s as easy as pulling up ChatGPT, telling it what’s going on, and trying out what it suggests.
That’s why I’ve trained Teal, your Tech Support chatbot specifically designed for freelancers and small business owners. Sign up below and I’ll send you the the link so you can start talking to her right now.
For a little context, here’s stuff I’ve been able to resolve thanks to a quick convo with ChatGPT:
How to create segments on my email platform
How (and where) to inject code on my website so that email sign-up shows up
Where to find the API (and what the heck that even means).
Resolving popups that told me I couldn’t do X until I resolved Y.
How to create a complex automation on my ClickUp.
How to turn a Google doc into a PDF
And so much more.
You’ve got this!